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A study of the reaction between 2,4-disubstituted-2,3-dihydro-1,5-benzothiazepines and ketenes generated in situ from chloro and dichloroacetyl chlorides

✍ Scribed by Qi-Yi Xing; Hong-Zhong Wang; Xin Zhou; Sheng Jin; Yue-Ming Li; Albert S. C. Chan

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 86 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380302

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✦ Synopsis

Abstract

In the presence of triethyl amine, the reaction of 2,4‐disubstituted‐2,3‐dihydro‐1,5‐benzothiazepine with chloro and dichloroacetyl chlorides produced not only the expected β‐lactam derivative of the benzo‐thiazepine, but also the ring opening product. Different results were obtained when the substituent at 2‐position of the benxothiazepine varied from methyl to aryl, and the substituent on the chloroacetyl chloride varied from H to Cl, or when carrying out the reaction at different temperatures. The structures of the obtained products and the reaction mechanism are discussed.

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